Stadium: Soldier Field
Referee: Victor Rivas Home Manager: Gregg Berhalter Away Manager: Oscar Pareja
| USA MLS | 2024/06/22 23:30 | Orlando City SC v Chicago Fire | L | 4-2 |
| USA MLS | 2024/05/30 00:30 | Chicago Fire v Orlando City SC | D | 1-1 |
| USA MLS | 2023/08/21 00:30 | Chicago Fire v Orlando City SC | L | 1-3 |
| USA MLS | 2023/07/01 23:30 | Orlando City SC v Chicago Fire | L | 3-1 |
| USA MLS | 2022/04/09 17:00 | Orlando City SC v Chicago Fire | L | 1-0 |
| USA MLS | 2022/03/05 23:00 | Chicago Fire v Orlando City SC | D | 0-0 |
| USA MLS | 2021/08/22 00:00 | Orlando City SC v Chicago Fire | L | 1-0 |
| USA MLS | 2021/07/08 00:00 | Chicago Fire v Orlando City SC | W | 3-1 |
| USA MLS | 2025/04/20 00:30 | Chicago Fire v FC Cincinnati | L | 2-3 |
| USA MLS | 2025/04/13 20:30 | Chicago Fire v Inter Miami CF | D | 0-0 |
| USA MLS | 2025/04/05 23:30 | New York Red Bulls v Chicago Fire | L | 2-1 |
| USA MLS | 2025/03/30 00:30 | Chicago Fire v CF Montreal | D | 1-1 |
| USA MLS | 2025/03/23 02:30 | Vancouver Whitecaps v Chicago Fire | W | 1-3 |
| USA MLS | 2025/03/15 18:30 | Toronto FC v Chicago Fire | W | 1-2 |
| USA MLS | 2025/03/09 01:30 | FC Dallas v Chicago Fire | W | 1-3 |
| USA MLS | 2025/03/02 01:30 | Chicago Fire v DC United | D | 2-2 |
| USA MLS | 2025/04/19 23:30 | CF Montreal v Orlando City SC | D | 0-0 |
| USA MLS | 2025/04/12 20:30 | Orlando City SC v New York Red Bulls | D | 0-0 |
| USA MLS | 2025/04/05 23:30 | Philadelphia Union v Orlando City SC | D | 0-0 |
| USA MLS | 2025/03/30 02:30 | LA Galaxy v Orlando City SC | W | 1-2 |
| USA MLS | 2025/03/22 23:30 | Orlando City SC v DC United | W | 4-1 |
| USA MLS | 2025/03/15 18:30 | New York Red Bulls v Orlando City SC | D | 2-2 |
| USA MLS | 2025/03/09 00:30 | New York City FC v Orlando City SC | L | 2-1 |
| USA MLS | 2025/03/02 00:30 | Orlando City SC v Toronto FC | W | 4-2 |